WO1994005630B1 - PROCEDES DE PREPARATION ET D'UTILISATION DE LA VITAMINE D2 1α,24(S)-DIHYDROXY - Google Patents
PROCEDES DE PREPARATION ET D'UTILISATION DE LA VITAMINE D2 1α,24(S)-DIHYDROXYInfo
- Publication number
- WO1994005630B1 WO1994005630B1 PCT/US1993/008141 US9308141W WO9405630B1 WO 1994005630 B1 WO1994005630 B1 WO 1994005630B1 US 9308141 W US9308141 W US 9308141W WO 9405630 B1 WO9405630 B1 WO 9405630B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dihydroxy vitamin
- converted
- vitamin
- formation
- hydroxyergosterol
- Prior art date
Links
- 229940088594 Vitamin Drugs 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000005755 formation reaction Methods 0.000 title 1
- 235000013343 vitamin Nutrition 0.000 title 1
- 239000011782 vitamin Substances 0.000 title 1
- 150000003722 vitamin derivatives Chemical class 0.000 title 1
- 229930003231 vitamins Natural products 0.000 title 1
- 239000000203 mixture Substances 0.000 claims 2
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 abstract 6
- 229960002061 Ergocalciferol Drugs 0.000 abstract 3
- 235000001892 vitamin D2 Nutrition 0.000 abstract 3
- 239000011653 vitamin D2 Substances 0.000 abstract 3
- LHXJPXPNCMSHPV-KAOCCWGPSA-N (3S,9S,10R,13R,14R,17R)-17-[(E,2R,5S)-5-hydroxy-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)/C=C/[C@@](C)(O)C(C)C)CC[C@H]33)C)C3=CC=C21 LHXJPXPNCMSHPV-KAOCCWGPSA-N 0.000 abstract 2
- HVAVRRBYXYEBNC-RKULPTJNSA-N (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R)-5-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/C(C)(O)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C HVAVRRBYXYEBNC-RKULPTJNSA-N 0.000 abstract 1
- DNVPQKQSNYMLRS-APGDWVJJSA-N Ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-APGDWVJJSA-N 0.000 abstract 1
- DNVPQKQSNYMLRS-LNHMRCHQSA-N Ergosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3C([C@H]4[C@@](C)([C@H]([C@@H](/C=C/[C@H](C(C)C)C)C)CC4)CC3)=CC=2)CC1 DNVPQKQSNYMLRS-LNHMRCHQSA-N 0.000 abstract 1
- 208000006641 Skin Disease Diseases 0.000 abstract 1
- 201000011431 calcium metabolism disease Diseases 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Abstract
Cette invention concerne l'utilisation de la vitamine D2 1α,24(S)-dihydroxy comme composé actif dans des compositions pharmaceutiques employées pour traiter des dérèglements du métabolisme du calcium et diverses affections cutanées. Cette invention concerne également la préparation de vitamine D2 1α,24(S)-dihydroxy de synthèse avec de l'ergostérol comme matière de départ qu'on transforme en six étapes en 24-hydroxyergostérol. On irradie le 24-hydroxyergostérol et on le transforme thermiquement en vitamine D2 24-hydroxy qu'on transforme en six étapes en vitamine D2 1α,24(S)-dihydroxy. Les synthèses produisent également de nouveaux intermédiaires.
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002121689A CA2121689C (fr) | 1992-08-28 | 1993-08-30 | 1.alpha.,24(s)-dihydroxy vitamine d2, sa formation et son utilisation |
EP93921243A EP0614456B1 (fr) | 1992-08-28 | 1993-08-30 | Procedes de preparation et d'utilisation de la vitamine 1alpha,24(s)-dihydroxy d2 |
DE69325253T DE69325253T2 (de) | 1992-08-28 | 1993-08-30 | 1alpha,24(s)-dihydroxy vitamin d2, seine synthese und verwendung |
DK93921243T DK0614456T3 (da) | 1992-08-28 | 1993-08-30 | 1alfa,24(S)-dihydroxy-vitamin D2, dets fremstilling og anvendelse |
AU48411/93A AU4841193A (en) | 1992-08-28 | 1993-08-30 | 1alpha,24(S)-dihydroxy vitamin D2, its formation and use |
JP50736194A JP3179495B2 (ja) | 1992-08-28 | 1993-08-30 | 1α,24(S)−ジヒドロキシビタミンD▲下2▼の調製及び使用方法 |
GR990402020T GR3030939T3 (en) | 1992-08-28 | 1999-08-10 | 1-g(a),24(S)-DIHYDROXY VITAMIN D 2?, ITS FORMATION AND USE. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US94024692A | 1992-08-28 | 1992-08-28 | |
US07/940,246 | 1992-08-28 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1994005630A1 WO1994005630A1 (fr) | 1994-03-17 |
WO1994005630B1 true WO1994005630B1 (fr) | 1994-04-14 |
Family
ID=25474483
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1993/008141 WO1994005630A1 (fr) | 1992-08-28 | 1993-08-30 | PROCEDES DE PREPARATION ET D'UTILISATION DE LA VITAMINE D2 1α,24(S)-DIHYDROXY |
Country Status (11)
Country | Link |
---|---|
US (1) | US6143910A (fr) |
EP (1) | EP0614456B1 (fr) |
JP (1) | JP3179495B2 (fr) |
AT (1) | ATE181062T1 (fr) |
AU (2) | AU4841193A (fr) |
CA (1) | CA2121689C (fr) |
DE (1) | DE69325253T2 (fr) |
DK (1) | DK0614456T3 (fr) |
ES (1) | ES2134267T3 (fr) |
GR (1) | GR3030939T3 (fr) |
WO (1) | WO1994005630A1 (fr) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5602116A (en) * | 1988-08-02 | 1997-02-11 | Bone Care International, Inc. | Method for treating and preventing secondary hyperparathyroidism |
US6538037B2 (en) | 1991-01-08 | 2003-03-25 | Bone Care International, Inc. | Methods for preparation and use of 1α,24(S)-dihydroxyvitamin D2 |
US6376479B1 (en) | 1995-04-03 | 2002-04-23 | Bone Care International, Inc. | Method for treating and preventing hyperparathyroidism |
US6242434B1 (en) * | 1997-08-08 | 2001-06-05 | Bone Care International, Inc. | 24-hydroxyvitamin D, analogs and uses thereof |
TW584627B (en) * | 1996-07-01 | 2004-04-21 | Chugai Pharmaceutical Co Ltd | The method for purifying vitamin D derivatives and its crystalline products |
US6573256B2 (en) | 1996-12-30 | 2003-06-03 | Bone Care International, Inc. | Method of inhibiting angiogenesis using active vitamin D analogues |
US6503893B2 (en) * | 1996-12-30 | 2003-01-07 | Bone Care International, Inc. | Method of treating hyperproliferative diseases using active vitamin D analogues |
US20020128240A1 (en) * | 1996-12-30 | 2002-09-12 | Bone Care International, Inc. | Treatment of hyperproliferative diseases using active vitamin D analogues |
US6566353B2 (en) | 1996-12-30 | 2003-05-20 | Bone Care International, Inc. | Method of treating malignancy associated hypercalcemia using active vitamin D analogues |
CA2326117A1 (fr) * | 1998-03-27 | 1999-10-07 | Oregon Health Sciences University | Vitamine d et ses analogues pour le traitement de tumeurs et d'autres troubles d'hyperproliferation |
US6362350B1 (en) * | 1999-07-01 | 2002-03-26 | Wisconsin Alumni Research Foundation | Crystalline 1α, 24(S)-dihydroxyvitamin D2 and method of purification thereof |
JP2004504295A (ja) * | 2000-07-18 | 2004-02-12 | ボーン ケア インターナショナル インコーポレイテッド | 安定化1α−ヒドロキシビタミンD |
BRPI0114927B8 (pt) * | 2000-10-27 | 2021-05-25 | Leo Pharma As | composição de gel farmacêutica não aquosa para aplicação na pele, e, uso de uma composição |
US7094775B2 (en) * | 2004-06-30 | 2006-08-22 | Bone Care International, Llc | Method of treating breast cancer using a combination of vitamin D analogues and other agents |
WO2009100258A1 (fr) * | 2008-02-05 | 2009-08-13 | Hollis-Eden Pharmaceuticals, Inc. | Formes pharmaceutiques à l'état solide |
KR101841260B1 (ko) * | 2016-11-25 | 2018-03-23 | 정미영 | 재난 대피용 테이블 장치 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4670190A (en) * | 1973-01-10 | 1987-06-02 | Hesse Robert H | 1-α-hydroxy vitamin D compounds and process for preparing same |
US3880894A (en) * | 1974-05-24 | 1975-04-29 | Wisconsin Alumni Res Found | 1,25-Dihydroxyergocalciferol |
US4022891A (en) * | 1974-06-18 | 1977-05-10 | Teijin Limited | Novel 1α,24-dihydroxycholecalciferol compositions, novel precursors thereof, and processes for preparing them |
GB1583749A (en) * | 1976-06-03 | 1981-02-04 | Res Inst Medicine Chem | Vitamin d derivatives |
US4195027A (en) * | 1978-01-16 | 1980-03-25 | Wisconsin Alumni Research Foundation | Process for preparing 1α-hydroxylated compounds |
US4338250A (en) * | 1981-04-27 | 1982-07-06 | Wisconsin Alumni Research Foundation | 1-Hydroxylation process |
US4719205A (en) * | 1984-01-30 | 1988-01-12 | Wisconsin Alumini Research Foundation | Side-chain unsaturated 1-hydroxyvitamin D compounds |
US4719204A (en) * | 1984-03-05 | 1988-01-12 | Wisconsin Alumni Research Foundation | Fowl bone mineralization with 28-NOR 1α-hydroxyvitamin D2 analogs |
US5104864A (en) * | 1988-08-02 | 1992-04-14 | Bone Care International, Inc. | Method for treating and preventing loss of bone mass |
US5098899A (en) * | 1989-03-06 | 1992-03-24 | Trustees Of Boston University | Method for therapeutically treating psoriatic arthritis using vitamin D analogues and metabolites |
US4973584A (en) * | 1989-03-09 | 1990-11-27 | Deluca Hector F | Novel 1α-hydroxyvitamin D2 epimer and derivatives |
US5260290A (en) * | 1990-02-14 | 1993-11-09 | Wisconsin Alumni Research Foundation | Homologated vitamin D2 compounds and the corresponding 1α-hydroxylated derivatives |
WO1992012165A1 (fr) * | 1991-01-08 | 1992-07-23 | Lunar Corporation | PROCEDES DE PREPARATION ET UTILISATION DE LA VITAMINE 1α,24-DIHYDROXY D¿2? |
-
1993
- 1993-08-30 DE DE69325253T patent/DE69325253T2/de not_active Expired - Lifetime
- 1993-08-30 JP JP50736194A patent/JP3179495B2/ja not_active Expired - Fee Related
- 1993-08-30 EP EP93921243A patent/EP0614456B1/fr not_active Expired - Lifetime
- 1993-08-30 AU AU48411/93A patent/AU4841193A/en not_active Abandoned
- 1993-08-30 DK DK93921243T patent/DK0614456T3/da active
- 1993-08-30 AT AT93921243T patent/ATE181062T1/de not_active IP Right Cessation
- 1993-08-30 ES ES93921243T patent/ES2134267T3/es not_active Expired - Lifetime
- 1993-08-30 CA CA002121689A patent/CA2121689C/fr not_active Expired - Lifetime
- 1993-08-30 WO PCT/US1993/008141 patent/WO1994005630A1/fr active IP Right Grant
-
1997
- 1997-02-21 AU AU14864/97A patent/AU1486497A/en not_active Abandoned
-
1998
- 1998-12-14 US US09/211,984 patent/US6143910A/en not_active Expired - Lifetime
-
1999
- 1999-08-10 GR GR990402020T patent/GR3030939T3/el unknown
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